Insect repellents



Patented Sept. 29, 1953 INSECT REPELLENTS Melvin S. Newman, Columbus,Ohio, and William B. Wheatley, Syracuse, N. Y., assignors to the UnitedStates of America as represented by the Secretary of the Army NoDrawing. Original application December 29,

1948, Serial No. 68,043. Divided and this application November 15, 1950,Serial No. 204,499

2 Claims.

This application is a division of our application Serial No. 68,043,filed December 29, 1948, for

Insect Repellents (now abandoned).

This invention relates to insect repellents.

We have found that the application of diols of the general formulaA(OH)2, in which A is an unsaturated aliphatic hydrocarbon radicalhaving from to 14 carbon atoms, including an open chain of from 8 to 10carbon atoms, characterized by a double or triple carbon to carbon bond,and in which the hydroxyl groups are alcoholic and attached to differentcarbon atoms on either side of the multiple bond, when applied to thehuman skin or to a fabric, afford effective protection against insectbites, by repelling insects, particularly Aedes aegypti and Anophelesqua/drimaculatus.

Tests to measure the repellency of the abovementioned compounds againstinsects by skin application were conducted by smearing the compound onthe arms of test personnel, who then thrust their arms into cagescontaining insects. Th arms were exposed for 30-minute intervals at 3minutes each until the first insect bite.

Tests to measure the repellency of fabrics impregnated with theabove-mentioned compounds against insects were conducted by uniformlyimpregnating mercerized cotton hose with the compound at a rateequivalent to 3.3 gm. per sq. ft., drawing the dried hose over the armsof test personnel, who then thrust their covered arms into cagescontaining insects for 1 to 2 minutes.

The following tables illustrate the results obtained by the above testmethods against Aedes aegypti and Anopheles quadrimaculatus, as ex- 2Table II.

pregnated Fab- 3,6-dimethyl-4-0ctynediol-3.6 over 10 days.

2,5,7-trimcthyl-Socty11ediol-2,5. D 3,6,8-trin1ethyl-4-nonynediol-3,6Do. 2,4,7,Q-tetramethyl-5-decyncdiol-4,7 Do.

It will be noted that in the unsaturated open chains of the compoundslisted in Tables I and II, methyl substituents are attached to the samecarbons as the alcoholic hydroxyl groups. Thus the triple-bond diolscontemplated by the present invention may be represented by the generalformula and the double-bonded diols by the general formula wherein a;and y are integers greater than 1.

For ease of application, the unsaturated aliphatic hydrocarbon diolscontemplated by the present invention may be incorporated in a suitableinert liquid or solid carrier such as mineral oil, alcohol, petrolatum,etc. For facile and uniform fabric impregnation, they may be applied inan inert solvent, such as alcohol, ether, etc.

Having thus described our invention,

We claim:

1. An Aedes aegypti repellent composition comprising atrimethyl-octene-diol in which the hydroxyl groups ar alcoholic andattached to methyl-substituent-carrying carbon atoms on either side ofthe double bond, in a non-toxic insectrepellent-adjuvant as a carriertherefor.

2. An Aedes aegypti repellent composition comprising2,5,7-trimethyl-3-octenediol-2,5 in a nontoxic insect-repellent-adjuvantas a carrier therefor.

MELVIN S. NEWMAN. WILLIAM B. WHEA'I'LEY.

(References on following page) References Cited in the file of thispatent UNITED STATES PATENTS OTHER REFERENCES OSRD, Insect ControlComittee Report No, 28, Interim Report No. 0-94; May 18, 1945.Particularly Pa e 34, Orlando No. 0-4356, 2,5-dimethyl- 43-hexene-2,5-diol. Also, pages 15, 39 and 48, Orlando Nos. 0-7159,0-7159 and 0-7095, respectively, for2,4,'7,9-tetra.methyl-5-decynediol-4,7 and 2,5-dimethyl-3-hexyndiol-2,5(in triacetin soln).

Linduska, Flea Repellents for Use on Clothing. Journal Econ. Entomology,December 1946, pages 767 to 769, especially at page 768, column 2 2,5,7-trimethy1-3-octynediol-2,5.

1. AN AEDES AEGYPTI REPELLENT COMPOSITION COMPRISING ATRIMETHYL-OCTENE-DIOL IN WHICH THE HYDROXYL GROUPS ARE ALCOHOLIC ANDATTACHED TO METHYL-SUBSTITUENT-CARRYING CARBON ATOMS ON EITHER SIDE OFTHE DOUBLE BOND, IN A NON-TOXIC INSECTREPELLENT-ADJUVANT AS A CARRIERTHEREFOR.